DD297955A5 - Verfahren zur herstellung chlorierter diphenylether - Google Patents

Verfahren zur herstellung chlorierter diphenylether Download PDF

Info

Publication number: DD297955A5
Authority: DD; German Democratic Republic
Prior art keywords: dichlorobenzene; phenolate; formula; mol; phenol
Prior art date: 1989-06-09

Application number

DD90341409A

Other languages

German (de)

English (en)

Inventor

Alfons Klein

Helmut Fiege

Joachim George

Original Assignee

Bayer Aktiengesellschaft,De

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-06-09

Filing date

1990-06-07

Publication date

1992-01-30

1990-06-07 Application filed by Bayer Aktiengesellschaft,De filed Critical Bayer Aktiengesellschaft,De

1992-01-30 Publication of DD297955A5 publication Critical patent/DD297955A5/de

Links

239000000460 chlorine Substances 0.000 title claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 title claims abstract description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title abstract description 10
238000004519 manufacturing process Methods 0.000 title description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 title 1
229940031826 phenolate Drugs 0.000 claims abstract description 17
-1 alkali metal cation Chemical group 0.000 claims abstract description 16
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims abstract description 16
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims abstract description 11
229940117389 dichlorobenzene Drugs 0.000 claims abstract description 10
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 2
239000003054 catalyst Substances 0.000 abstract description 9
239000003880 polar aprotic solvent Substances 0.000 abstract description 9
229910052751 metal Inorganic materials 0.000 abstract description 5
239000002184 metal Substances 0.000 abstract description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 8
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000004707 phenolate Chemical class 0.000 description 3
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000006887 Ullmann reaction Methods 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
150000004816 dichlorobenzenes Chemical class 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000005171 halobenzenes Chemical class 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
MWKULKMSBBSGTP-UHFFFAOYSA-N 1-chloro-2-(4-chlorophenoxy)benzene Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CC=C1Cl MWKULKMSBBSGTP-UHFFFAOYSA-N 0.000 description 1
HPRGYUWRGCTBAV-UHFFFAOYSA-N 1-chloro-3-(4-chlorophenoxy)benzene Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CC(Cl)=C1 HPRGYUWRGCTBAV-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical class CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 description 1
HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000003517 branched hexyloxy group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical class [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
238000005648 named reaction Methods 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD90341409A 1989-06-09 1990-06-07 Verfahren zur herstellung chlorierter diphenylether DD297955A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3918897A DE3918897A1 (de)	1989-06-09	1989-06-09	Verfahren zur herstellung chlorierter diphenylether

Publications (1)

Publication Number	Publication Date
DD297955A5 true DD297955A5 (de)	1992-01-30

Family

ID=6382443

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90341409A DD297955A5 (de)	1989-06-09	1990-06-07	Verfahren zur herstellung chlorierter diphenylether

Country Status (4)

Country	Link
EP (1)	EP0401626B1 (fr)
JP (1)	JP2786315B2 (fr)
DD (1)	DD297955A5 (fr)
DE (2)	DE3918897A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19541749C1 (de) *	1995-11-09	1997-05-22	Daimler Benz Ag	Servolenkung für Kraftfahrzeuge
AU6466899A (en) *	1998-10-06	2000-04-26	Ciba Specialty Chemicals Holding Inc.	A process for the preparation of 4,4'-dihalogen-o-hydroxydiphenyl compounds
CN105198713B (zh) *	2015-09-30	2017-05-10	黄山学院	一种利用微波催化合成3，4’‑二氯二苯醚的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1643344A1 (de) *	1967-08-18	1971-06-09	Bayer Ag	Verfahren zur Herstellung von Arylaethern bzw.-polyaethern
DE3040849A1 (de) *	1980-10-30	1982-06-09	Hoechst Ag, 6000 Frankfurt	Verfahren zur herstellung von diphenylaethern
US4766253A (en) *	1987-05-04	1988-08-23	Ciba-Geigy Corporation	Process for preparing chlorinated diphenyl ethers

1989
- 1989-06-09 DE DE3918897A patent/DE3918897A1/de not_active Withdrawn
1990
- 1990-05-26 EP EP90110029A patent/EP0401626B1/fr not_active Expired - Lifetime
- 1990-05-26 DE DE90110029T patent/DE59004278D1/de not_active Expired - Fee Related
- 1990-06-06 JP JP2146374A patent/JP2786315B2/ja not_active Expired - Lifetime
- 1990-06-07 DD DD90341409A patent/DD297955A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE3918897A1 (de)	1990-12-13
EP0401626B1 (fr)	1994-01-19
EP0401626A3 (fr)	1991-05-22
DE59004278D1 (de)	1994-03-03
JPH0324030A (ja)	1991-02-01
JP2786315B2 (ja)	1998-08-13
EP0401626A2 (fr)	1990-12-12

Legal Events

Date	Code	Title	Description
1996-08-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0297028B1 (fr)	1993-08-18	Procédé pour la préparation de l'éther diphényle chloré
EP0364877A1 (fr)	1990-04-25	Procédé pour la préparation du Bis(4-chlorophenyl) sulfone
EP0175151B1 (fr)	1989-01-18	2,4-Dichloro-3-alkyl-6-nitrophénols et un procédé pour leur préparation
CH664954A5 (de)	1988-04-15	Verfahren zur herstellung von tetrachlor-2-cyanbenzoesaeurealkylestern.
DE876690C (de)	1953-05-18	Verfahren zur Herstellung von Ketonen aus ªÏ-trihalogenmethylsubstituierten aromatischen Verbindungen
DD297955A5 (de)	1992-01-30	Verfahren zur herstellung chlorierter diphenylether
EP0621262B1 (fr)	1996-09-11	Procédé de préparation d'esters très purs de l'acide 3-chloroanthranilique au départ de cet acide
DE3104388A1 (de)	1982-10-21	Verfahren zur herstellung von 1-alkyl-2-chlor-5-nitro-4-benzol-sulfonsaeuren
EP0498847B1 (fr)	1994-09-14	Procede de preparation de 1,4-bis-(4-hydroxybenzoyl)-benzol
DE2624360A1 (de)	1976-12-16	Verfahren zur herstellung von gegebenenfalls substituiertem 3-phenoxybenzaldehyd
DE2019196B2 (de)	1974-03-28	Verfahren zur Herstellung von 4-Meftoxy-2,6-di-tert-butylphenoL
DE3813452A1 (de)	1988-11-03	Verfahren zur herstellung von trifluormethylbenzoesaeure aus hexafluorxylol
DD146599A5 (de)	1981-02-18	Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamid
DE3200431A1 (de)	1983-07-21	Verfahren zur herstellung von 4-fluor-3-phenoxytoluol
EP0342532B1 (fr)	1993-01-07	Procédé pour la préparation du 4-chloro-2-méthyl-5-nitro-phénol
EP0212608A1 (fr)	1987-03-04	Procédé pour la préparation de sulfures d'halogénophényle et d'hydroxyéthyle et de leurs produits d'oxydation
EP0075613B1 (fr)	1985-06-12	Procédé de préparation de N-(-1-formylamido-2,2,2-trichloroéthyl)-morpholine
DE19934231B4 (de)	2004-02-19	Verfahren zur Herstellung von 1-substituierten 5-Hydroxy-imidazolin-2,4-dionen und 1-substituierten 5-Alkoxy-imidazolin-2,4-dionen
EP4688764A2 (fr)	2026-02-11	Procédé de production du méthyl-4-isocyanatosulfonyl-5-méthyl-thiophène-3-carboxylate
DE2133897C3 (de)	1980-11-13	Verfahren zur Herstellung von 4,4'-Dibrombenzil
EP0000567A1 (fr)	1979-02-07	Procédé de préparation de 2,6-di-tert. alkyle-4-alkylidène-2,5-cyclohexadiènones
EP0052817A1 (fr)	1982-06-02	Procédé pour la préparation de 4-chloro-2,6-dialcoyl anilines
DE2035657B2 (de)	1975-09-18	27.03.70 Japan 26217-70 Verfahren zur Herstellung von 4-Halogen-5-sulfamoylanthranilsäureaniliden
DE1294970B (de)	1969-05-14	Verfahren zur Herstellung von substituierten 6, 11-Dihydrodibenzo[b, e]-oxepin- bzw.-thiepin-11-onen
EP0212607A1 (fr)	1987-03-04	Procédé pour la préparation de sulfures d'halogénophényle et d'hydroxyéthyle et de leurs produits d'oxydation